diff --git a/crates/chat_ui/src/lib.rs b/crates/chat_ui/src/lib.rs
index 3622e41b..0ad30ce3 100644
--- a/crates/chat_ui/src/lib.rs
+++ b/crates/chat_ui/src/lib.rs
@@ -3,7 +3,7 @@ use std::path::PathBuf;
 use std::sync::{Arc, LazyLock, RwLock};
 
 pub use actions::*;
-use anyhow::{Context as AnyhowContext, Error};
+use anyhow::Error;
 use chat::{ChatRegistry, Message, Room, RoomEvent, SendReport, SendStatus};
 use common::{TimestampExt, coop_cache};
 use futures::lock::Mutex;
@@ -709,13 +709,15 @@ impl ChatPanel {
         });
 
         self.tasks.push(cx.spawn_in(window, async move |this, cx| {
+            // Selecting no file means the prompt was cancelled
+            let Some(path) = path.await??.and_then(|mut paths| paths.pop()) else {
+                return Ok(());
+            };
+
             this.update(cx, |this, cx| {
                 this.set_uploading(true, cx);
             })?;
 
-            let mut paths = path.await??.context("Not found")?;
-            let path = paths.pop().context("No path")?;
-
             // Upload the file, encrypted when it is the whole message
             let result = if encrypted {
                 upload_encrypted(server, path.clone(), cx)
diff --git a/crates/workspace/src/panels/profile.rs b/crates/workspace/src/panels/profile.rs
index a944c9cf..c9e46d93 100644
--- a/crates/workspace/src/panels/profile.rs
+++ b/crates/workspace/src/panels/profile.rs
@@ -1,6 +1,6 @@
 use std::str::FromStr;
 
-use anyhow::{Context as AnyhowContext, Error};
+use anyhow::Error;
 use gpui::{
     AnyElement, App, AppContext, ClipboardItem, Context, Entity, EventEmitter, FocusHandle,
     Focusable, IntoElement, ParentElement, PathPromptOptions, Render, SharedString, Styled, Task,
@@ -167,13 +167,15 @@ impl ProfilePanel {
         });
 
         self.tasks.push(cx.spawn_in(window, async move |this, cx| {
+            // Selecting no file means the prompt was cancelled
+            let Some(path) = path.await??.and_then(|mut paths| paths.pop()) else {
+                return Ok(());
+            };
+
             this.update(cx, |this, cx| {
                 this.set_uploading(true, cx);
             })?;
 
-            let mut paths = path.await??.context("Not found")?;
-            let path = paths.pop().context("No path")?;
-
             // Upload via blossom client
             match upload(server, path, cx).await {
                 Ok(url) => {